2-Chloroquinoline → 10-(2-Quinolinyloxy)decan-1-ol

HRID 1196560Notes

Reaction equation

[CH2:1]([OH:12])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][OH:11].Cl[C:14]1[CH:23]=[CH:22][C:21]2[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=2)[N:15]=1>>[N:15]1[C:16]2[C:21](=[CH:20][CH:19]=[CH:18][CH:17]=2)[CH:22]=[CH:23][C:14]=1[O:12][CH2:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][OH:11]

Participants

Reactant 2

HCID 119282-Chloroquinoline

HCID 371531,10-Decanediol

Product 1

HCID 1989867210-(2-Quinolinyloxy)decan-1-ol

Procedure

1,10-Decanediol (ex. Lancaster) was reacted with 2-chloroquinoline, by analogy with compound 33, step (i), to give 10-(2-quinolinyloxy)decan-1-ol. The latter was subjected to Swern oxidation (cf. example XIV) and the aldehyde reacted with ethyl fluoroacetate and diethyl oxalate to give (2Z) ethyl 2-fluoro-12-(2-quinoliny-loxy)dodec-2-enoate. The latter was converted to the title compound by analogy with compound 33, step (iv).

Sources & evidence

ORD record: ord-b79c46f172cc4915abfeeb2046e9c575
Source dataset: uspto-grants-1992_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05114940

Reaction notes

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